Compare Vacation Rentals & Rent By Owner Homes in Chestnut Hill, Massachusetts, USA
About Chestnut Hill Vacation Rentals
With more than 642 Chestnut Hill vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Chestnut Hill.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Chestnut Hill, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Chestnut Hill. Places to stay near Chestnut Hill are 585.29 ft² on average, with prices averaging US $344 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in Chestnut Hill with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Other Places to Stay in Chestnut Hill, MA
Frequently Asked Questions About Chestnut Hill?
What are the top vacation rentals in Chestnut Hill?
- Airy new apt for 2-6. Off-street parking. Walk to shops/restaurants/subway/bus
- Boston-Modern Spacious Family Friendly Apartment w/Parking
- Rare Find in Boston's Hippest Neighborhood
- The Inn at Newton Highlands, boutique apartment-hotel
- The Inn at Newton Highlands, boutique apartment-hotel
- A Village Bed and Breakfast
- Terrific vacation house only 4.5 miles away from downtown Boston
- The Inn at Newton Highlands, Suite 2, Apartment-Hotel
- Remodeled Spacious Apartment in Perfect Location
- Clean, Spacious and Located Steps Away From the MBTA!
How many Rentbyowner vacation rentals are available in Chestnut Hill?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 642 in the Chestnut Hill area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Chestnut Hill.
Nearby Neighborhood (8)
| Neighborhood | Property Count |
|---|---|
| Brighton Vacation Rentals in Boston, Massachusetts | 132 |
| Cleveland Circle Vacation Rentals in Boston, Massachusetts | 132 |
| Commonwealth Vacation Rentals in Boston, Massachusetts | 145 |
| Newton Corner Vacation Rentals in Boston, Massachusetts | 497 |
| Woodland Heath Vacation Rentals in Boston, Massachusetts | 814 |
| South Brookline Vacation Rentals in Boston, Massachusetts | 501 |
| Thompsonville Vacation Rentals in Boston, Massachusetts | 358 |
| Brook Farm Vacation Rentals in Boston, Massachusetts | 176 |
